1-Ethyl-3-(3'-dimethylaminopropyl)carbodiimide → 4,5-bis(nitrooxy)pentyl (2Z)-4(acetyloxy)-3-[4-(methylsulfonyl)phenyl]-2-phenylbut-2-enoate

HRID 1437607Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1437607
[C:1]([O:4][CH2:5]/[C:6](/[C:17]1[CH:22]=[CH:21][C:20]([S:23]([CH3:26])(=[O:25])=[O:24])=[CH:19][CH:18]=1)=[C:7](/[C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1)\[C:8]([OH:10])=[O:9])(=[O:3])[CH3:2].[N+:27]([O:30][CH:31]([CH2:36][O:37][N+:38]([O-:40])=[O:39])[CH2:32][CH2:33][CH2:34]O)([O-:29])=[O:28].CCN=C=NCCCN(C)C>C(Cl)Cl.CN(C1C=CN=CC=1)C>[C:1]([O:4][CH2:5]/[C:6](/[C:17]1[CH:22]=[CH:21][C:20]([S:23]([CH3:26])(=[O:25])=[O:24])=[CH:19][CH:18]=1)=[C:7](/[C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1)\[C:8]([O:10][CH2:34][CH2:33][CH2:32][CH:31]([O:30][N+:27]([O-:29])=[O:28])[CH2:36][O:37][N+:38]([O-:40])=[O:39])=[O:9])(=[O:3])[CH3:2]

Komponenten

6

Edukt 3

HCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 11617716(Z)-4-Acetoxy-3-(4-(methylsulfonyl) phenyl)-2-phenylbut-2-enoic acidHCID 579416234,5-Bis(nitrooxy)pentyl alcohol

Produkt 1

HCID 114444494,5-bis(nitrooxy)pentyl (2Z)-4(acetyloxy)-3-[4-(methylsulfonyl)phenyl]-2-phenylbut-2-enoateAusbeute 38,4 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 142844-(Dimethylamino)pyridineKatalysatorHCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

To a solution of 1.72 g of (2Z)-4-(acetyloxy)-3-[4-(methylsulfonyl)phenyl]-2-phenylbut-2-enoic acid in 20 mL of CH2Cl2 at 0° C. was added 1.06 g of 4,5-bis(nitrooxy)pentyl alcohol, 225 mg of DMAP and 970 mg of EDCI. The mixture was stirred at RT for 2 h then quenched by addition of NH4Cl sat., extracted with EtOAc, washed with NaHCO3 sat., brine and dried over sodium sulfate. Purification by flash chromatography afforded 1 g of the titled compound as a white solid. 1H NMR (acetone-d6, 500 MHz): δ 7.77 (d, 2H), 7.43 (d, 2H), 7.18-7.16 (m, 3H), 7.08 (dd, 2H), 5.53-5.50 (m, 1H), 5.20 (s, 1H), 4.97 (dd, 1H), 4.69 (dd, 1H), 4.31 (m, 2H), 3.05 (s, 2H), 1.89 (m, 7H).

Aufarbeitung

  1. customthen quenched by addition of NH4Cl sat.
  2. extractionextracted with EtOAc
  3. washwashed with NaHCO3 sat., brine
  4. dry with materialdried over sodium sulfate
  5. customPurification by flash chromatography

Quellen und Nachweise

ORD-Eintrag
ord-03c2848ff5af4a138c5ef799bdecf1e1
Quelldatensatz
uspto-grants-2009_11
Patentnummer
US07622502B2

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